Gold- and Brønsted Acid-Catalyzed Cycloisomerization of 1,8-Diynyl Vinyl Acetates to Bicyclo[2.2.1]hept-2-en-7-ones

Xiaoyu Chen; David Philip Day; Wan Teng Teo; Philip Wai Hong Chan

doi:10.1021/acs.orglett.6b03049

Gold- and Brønsted Acid-Catalyzed Cycloisomerization of 1,8-Diynyl Vinyl Acetates to Bicyclo[2.2.1]hept-2-en-7-ones

Xiaoyu Chen
, David Philip Day
, Wan Teng Teo
, Philip Wai Hong Chan

School of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

29 Citations (Scopus)

Abstract

A synthetic method for the efficient assembly of bicyclo[2.2.1]hept-2-en-7-ones that relies on gold(I)-catalyzed Rautenstrauch rearrangement followed by Brønsted acid-mediated formal [3 + 2]-cycloaddition/deacetylation of 1,8-diynyl vinyl acetates at room temperature under atmospheric conditions is described.

Original language	English
Pages (from-to)	5936-5939
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.6b03049
Publication status	Published - 18 Nov 2016

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10.1021/acs.orglett.6b03049

53175730-oaAccepted author manuscript, 443 KBLicence: Unspecified

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title = "Gold- and Br{\o}nsted Acid-Catalyzed Cycloisomerization of 1,8-Diynyl Vinyl Acetates to Bicyclo[2.2.1]hept-2-en-7-ones",

abstract = "A synthetic method for the efficient assembly of bicyclo[2.2.1]hept-2-en-7-ones that relies on gold(I)-catalyzed Rautenstrauch rearrangement followed by Br{\o}nsted acid-mediated formal [3 + 2]-cycloaddition/deacetylation of 1,8-diynyl vinyl acetates at room temperature under atmospheric conditions is described.",

author = "Xiaoyu Chen and Day, \{David Philip\} and Teo, \{Wan Teng\} and Chan, \{Philip Wai Hong\}",

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language = "English",

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journal = "Organic Letters",

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AU - Chen, Xiaoyu

AU - Day, David Philip

AU - Teo, Wan Teng

AU - Chan, Philip Wai Hong

PY - 2016/11/18

Y1 - 2016/11/18

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AB - A synthetic method for the efficient assembly of bicyclo[2.2.1]hept-2-en-7-ones that relies on gold(I)-catalyzed Rautenstrauch rearrangement followed by Brønsted acid-mediated formal [3 + 2]-cycloaddition/deacetylation of 1,8-diynyl vinyl acetates at room temperature under atmospheric conditions is described.

UR - https://www.scopus.com/pages/publications/84996553542

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DO - 10.1021/acs.orglett.6b03049

M3 - Article

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IS - 22

ER -

Gold- and Brønsted Acid-Catalyzed Cycloisomerization of 1,8-Diynyl Vinyl Acetates to Bicyclo[2.2.1]hept-2-en-7-ones

Abstract

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New Efficient Alkyne Cyclization Strategies for Complex Molecule Synthesis

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Gold- and Brønsted Acid-Catalyzed Cycloisomerization of 1,8-Diynyl Vinyl Acetates to Bicyclo[2.2.1]hept-2-en-7-ones

Abstract

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New Efficient Alkyne Cyclization Strategies for Complex Molecule Synthesis

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